The objective of the proposed work is to develop several boronic acid derivatives which can be used for affinity chromatography of certain enzymes and glycoproteins and for the detection and study of the environment of carbohydrates attached to proteins and/or cell surfaces. The design of these reagents rests on the well-known ability of boronic acids to esterify to cis-diols. A series of alkane and aromatic boronic acids will be made by methods described in the chemical literature; the pKa's, strengths of complex formation, and stabilities in water of these will be determined. The most suitable of these compounds will be attached to insoluble acrylamide or cellulose supports; these will be tested for their ability to bind glycoproteins selectively. The same supports will be tested, when saturated with selected diol-containing cofactors, for their usefulness in enzyme affinity chromatography. In addition suitable boronic acids will be derivatized with chromogenic, fluorogenic and spin-label groups. These derivatives will be evaluated for their abilities to bind to and to reflect local environments of glycoproteins and cell surfaces (sporulating Bacillus subtilis). Finally, certain boronic acids will be coupled to form water-soluble diboronic acids; these will be tested for their abilities to cross-link difunctional glycoproteins and to agglutinate cells.